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Compound Detail

CHEMBL227231

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CN1[C@H]2CC[C@@H]1[C@@H](c1ncc(-c3cccc(Br)c3)s1)[C@@H](c1ccc(Cl)cc1)C2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL227231
Phase Preclinical
Structure Type MOL
InChI Key DRLOWUSIOOIRRD-HIUFNZKISA-N
5
Targets
8
Activities
2
Assay Types
0
PK Parameters
4
Publications
0
Known Names

Molecular Properties

473.9
MW (Da)
6.96
ALogP
3
HBA
0
HBD
16.1
PSA (Ų)
0.41
QED
1
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C23H22BrClN2S
MW 473.87
Aromatic Rings 3
Heavy Atoms 28
NP-Likeness -0.52

Activity Summary

IC50 4 meas. best 7.75
Ki 4 meas. best 7.41

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sodium-dependent dopamine transporter
CHEMBL338
 IC50 7.75 7.75 18.0 1
Sodium-dependent dopamine transporter
CHEMBL238
 Ki 7.41 7.41 39.0 1
Sodium-dependent dopamine transporter
CHEMBL238
 IC50 7.2 7.2 63.0 1
Sodium-dependent serotonin transporter
CHEMBL313
 Ki 6.55 6.55 280.0 1
Sodium-dependent serotonin transporter
CHEMBL228
 Ki 5.82 5.82 1500.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
 IC50 5.64 5.64 2300.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
 Ki 5.6 5.6 2530.0 1
Sodium-dependent serotonin transporter
CHEMBL228
 IC50 5.4 5.4 4000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sodium-dependent dopamine transporter IC50 = 18.0 nM 7.75 Displacement of [3H]WIN-35428 from DAT in Sprague-Dawley rat brain 17602602
Sodium-dependent dopamine transporter Ki = 39.0 nM 7.41 Displacement of [125I]RTI-55 from human DAT expressed in HEK cells after 90 mins 17602602
Sodium-dependent dopamine transporter IC50 = 63.0 nM 7.2 Inhibition of human DAT in HEK cells assessed as [3H]dopamine reuptake 17602602
Sodium-dependent serotonin transporter Ki = 280.0 nM 6.55 Displacement of [3H]paroxetine from SERT in Sprague-Dawley rat brain 17602602
Sodium-dependent serotonin transporter Ki = 1500.0 nM 5.82 Displacement of [125I]RTI-55 from human SERT expressed in HEK cells after 90 min... 17602602
Sodium-dependent noradrenaline transporter IC50 = 2300.0 nM 5.64 Inhibition of human NET in HEK cells assessed as [3H]norepinephrine reuptake 17602602
Sodium-dependent noradrenaline transporter Ki = 2530.0 nM 5.6 Displacement of [125I]RTI-55 from human NET expressed in HEK cells after 90 mins 17602602
Sodium-dependent serotonin transporter IC50 = 4000.0 nM 5.4 Inhibition of human SERT in HEK cells assessed as [3H]serotonin reuptake 17602602

Literature References

PubMed DOI Target Context # Activities
17602602 10.1021/jm0703035 Sodium-dependent dopamine transporter 3
17602602 10.1021/jm0703035 Sodium-dependent serotonin transporter 3
17602602 10.1021/jm0703035 Sodium-dependent noradrenaline transporter 2
17602602 10.1021/jm0703035 Norepinephrine transporter 1

Data from ChEMBL 36 via Core Engine